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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:46:01 UTC
HMDB IDHMDB0014617
Secondary Accession Numbers
  • HMDB14617
Metabolite Identification
Common NameMethohexital
DescriptionMethohexital is only found in individuals that have used or taken this drug. It is an intravenous anesthetic with a short duration of action that may be used for induction of anesthesia. [PubChem]Methohexital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Structure
Data?1582753199
Synonyms
ValueSource
(+-)-5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)barbituric acidChEBI
5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-Allyl-1-methyl-5-(1-methyl-pent-2-ynyl)-pyrimidine-2,4,6-trioneChEBI
5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbituric acidChEBI
alpha-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbituric acidChEBI
MethohexitalumChEBI
MethohexitoneChEBI
MetohexitalChEBI
(+-)-5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)barbitateGenerator
(+-)-5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)barbitic acidGenerator
5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbitateGenerator
5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbitic acidGenerator
a-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitateGenerator
a-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitic acidGenerator
alpha-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitateGenerator
alpha-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitic acidGenerator
Α-DL-1-methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitateGenerator
Α-DL-1-methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbitic acidGenerator
MethodrexitoneHMDB
BrevitalMeSH, HMDB
Sodium, methohexitalMeSH, HMDB
BrietalMeSH, HMDB
Lilly brand OF methohexital sodiumMeSH, HMDB
Methohexital sodiumMeSH, HMDB
Brietal-sodiumMeSH, HMDB
Brevimytal natriumMeSH, HMDB
Jones brand OF methohexital sodiumMeSH, HMDB
Methohexital, monosodium saltMeSH, HMDB
Monosodium salt methohexitalMeSH, HMDB
Natrium, brevimytalMeSH, HMDB
Brietal sodiumMeSH, HMDB
Chemical FormulaC14H18N2O3
Average Molecular Weight262.3043
Monoisotopic Molecular Weight262.131742452
IUPAC Name5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
Traditional Namemethohexital
CAS Registry Number151-83-7
SMILES
CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O
InChI Identifier
InChI=1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)
InChI KeyNZXKDOXHBHYTKP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentBarbituric acid derivatives
Alternative Parents
Substituents
  • Barbiturate
  • N-acyl urea
  • Ureide
  • 1,3-diazinane
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.052 g/LNot Available
LogP1.8Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP10(2.43) g/LALOGPS
logP10(2.29) g/LChemAxon
logS10(-3.7) g/LALOGPS
pKa (Strongest Acidic)8.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity71.51 m³·mol⁻¹ChemAxon
Polarizability27.4 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+162.58831661259
DarkChem[M-H]-160.63931661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methohexital GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-4390000000-8c577a429e1b4575b6292017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methohexital GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methohexital GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methohexital GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fbc-9520000000-5141cdceea7f6d5013b02014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methohexital 35V, Positive-QTOFsplash10-00ya-3900000000-577a972e968dc27cf6a62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 10V, Positive-QTOFsplash10-03di-2090000000-43730b3bde391b731ebe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 20V, Positive-QTOFsplash10-00dl-3970000000-fc9a91490da8afc576f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 40V, Positive-QTOFsplash10-0f9x-9000000000-93587b41eae6b9864e812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 10V, Negative-QTOFsplash10-001i-2920000000-ad50a444d0a4a9a5af2c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 20V, Negative-QTOFsplash10-0a4l-4910000000-c5dc261173ac7024e26f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 40V, Negative-QTOFsplash10-0006-9200000000-7cedeac5d5e1a5954aa42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 10V, Negative-QTOFsplash10-03di-0090000000-c3de47045d3b9ea5dd1f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 20V, Negative-QTOFsplash10-03dl-4890000000-e57232418c552e436a952021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 40V, Negative-QTOFsplash10-015c-3910000000-34338787c291ec35bb4c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 10V, Positive-QTOFsplash10-03di-0190000000-859e807fb540e8aaf0912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 20V, Positive-QTOFsplash10-053r-0910000000-70fde9c253e18d4487912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methohexital 40V, Positive-QTOFsplash10-0udi-9300000000-67ceed0497570d0689e32021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00474 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00474 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00474
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8683
KEGG Compound IDC07844
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethohexital
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID102216
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1753031
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Koltchine VV, Ye Q, Finn SE, Harrison NL: Chimeric GABAA/glycine receptors: expression and barbiturate pharmacology. Neuropharmacology. 1996;35(9-10):1445-56. [PubMed:9014160 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]